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929016-96-6 (Pracinostat)

1

Identification

Pracinostat Pracinostat
Name Pracinostat
Formula C20H30N4O2
MW 358.48
CAS No. 929016-96-6
EINECS
Smiles ONC(/C=C/C1=CC=C2N(C(CCCC)=NC2=C1)CCN(CC)CC)=O
Synonyms SB939;SB-939;SB 939; (E)-3-(2-butyl-1-(2-(diethylamino)ethyl)-1H-benzo[d]imidazol-5-yl)-N-hydroxyacrylamide
InChI InChI=1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+
2

Introduction

Pracinostat(SB939) is a potent pan-HDAC inhibitor with IC50 of 40-140 nM with exception for HDAC6; has no activity against the class III isoenzyme SIRT I.

Background Information

A potent pan-HDAC inhibitor ......by AOBIOUS INC
SB939 is a novel potent and orally active histone deacetylase with high tumor exposure and efficacy in mouse models of colorectal cancer. The IC50 value for HDAC1 is 52 nM. In vitro, SB939 inhibits class I, II and IV HDACs, with no effects on other zinc binding enzymes, and shows significant antiproliferative activity against a wide variety of tumor cell lines. It has very favorable pharmacokinetic properties after oral dosing in mice, with >4-fold increased bioavailability and 3.3-fold increased half-life over suberoylanilide hydroxamic acid (SAHA). ......by AbMole BioScience
SB939 is an oral inhibitor of HDAC, selective for class I, II and IV HDACs and displays an IC50 value of 77 nM in an in vitro HDAC1 activity assay. ......by AdooQ BioScience, LLC
Description ......by Apexbio Technology LLC
Pracinostat (SB939) is an orally bioavailable, small-molecule histone deacetylase (HDAC) inhibitor with potential antineoplastic activity. Pracinostat inhibits HDACs, which may result in the accumulation of highly acetylated histones, followed by the indu ......by BOC Sciences
An orally available pan-histone deacetylase (HDAC) inhibitor binding all HDAC isozymes with similar affinity (Kis = 16-28 nM) with the exception of HDAC6 and 7 (Kis = 247 and 104 nM, respectively). SB 939 demonstrates good bioavailability in vivo and significantly inhibits tumor growth in various xenograft mouse models at doses ranging from 25-100 mg/kg. ......by BioVision, Inc.,
Pracinostat is a potent histone deacetylase (HDAC) inhibitor, with IC50s of 40-140 nM, used for cancer research. ......by MedChemexpress Co., Ltd.
Pracinostat, also known as SB939, is an orally bioavailable, small-molecule histone deacetylase (HDAC) inhibitor with potential antineoplastic activity. Pracinostat inhibits HDACs, which may result in the accumulation of highly acetylated histones, followed by the induction of chromatin remodeling; the selective transcription of tumor suppressor genes; the tumor suppressor protein-mediated inhibition of tumor cell division; and, finally, the induction of tumor cell apoptosis. In March 2014, pracinostat has granted Orphan Drug for acute myelocytic leukemia (AML) and for the treatment of T-cell lymphoma by the Food and Drug Administration. ......by MedKoo Biosciences, Inc.
Pracinostat (SB939) is a potent, orally active HDAC inhibitor that potently inhibits class I, II, and IV HDACsw with Ki of 15-100 nM, inhibits HDAC1 with IC50 of 77 nM; shows cellular potency against COLO 205 cells with IC50 of 0.56 uM; Pracinostat (SB939) is highly efficacious in in vivo tumor models (HCT-116, PC-3, A2780, MV4-11, Ramos), and has high and dose-proportional oral exposures and very good ADME, safety, and pharmaceutical properties; also is a potent inhibitor of the growth of Plasmodium falciparum asexual-stage parasites in vitro (IC50=100 to 200 nM), causing hyperacetylation of parasite histone and nonhistone proteins.Blood CancerPhase 3 Clinical ......by ProbeChem
PCI-34051 is a potent and specific HDAC8 inhibitor with IC50 of 10 nM in a cell-free assay. It has greater than 200-fold selectivity over HDAC1 and 6, more than 1000-fold selectivity over HDAC2, 3, and 10. ......by Selleck Chemicals LLC
Pracinostat(SB939) is a potent pan-HDAC inhibitor with IC50 of 40-140 nM with exception for HDAC6; has no activity against the class III isoenzyme SIRT I. ......by Target Molecule Corp.
3

Protocol(Only for Reference)

Cell Experiment

Cell lines Ovarian (A2780) , colon (HCT-116), and prostate (PC-3) cell lines
Conditions 96 h; IC50=0.48±0.21 μM (A2780), 0.48±0.27 μM (HCT-116), 0.34±0.06 μM (PC-3)
Method SB939 showed broad anti-proliferative activity against representative tumor cells from ovarian (A2780) , colon (HCT-116), and prostate (PC-3) with cellular IC50 values of 0.48±0.21, 0.48±0.27 and 0.34±0.06 μM, respectively.
Source Apexbio Technology LLC
Cell lines HCT116, A2780, ACHN, MCF7, HL-60, et al.
Conditions Dissolved in DMSO (stock concentration, 10 mM), final concentrations 1.5 nM to 100 μM; 96 hours
Method Cells are seeded in 96-well plates in the log growth phase at a predetermined optimal density, and rested for 24 hours (adherent cells) or 2 hours (suspension cells), respectively. They are exposed to different concentrations of SB939 for 96 hours. Cell proliferation assays are done using either the CyQUANT cell proliferation assay kit for adherent cells or the CellTiter96 Aqueous One solution cell proliferation kit for suspension cells.
Source Selleck Chemicals LLC

Animal Experiment

Animal Models BALB/c nude mice bearing HCT-116 human colon cancer xenografts, Male and APCmin mice
Dosage 25, 50, 75, or 100 mg/kg
Formulation Dissolved in DMSO and prepared in 0.5% methylcellulose (w/v) and 0.1% Tween-80 in water
Administration Oral gavage once daily
Source Selleck Chemicals LLC
4

Physical and Chemical Properties

Appearance:White to off-white solid EBNumber:EB000028599

Storage condition

Store at -20°C by Apexbio Technology LLC
Storage condition:Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). Stock solution storage:0 - 4 C for short term (days to weeks), or -20 C for long term (months). Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. by MedKoo Biosciences, Inc.

Solubility

Soluble in DMSO > 10 mM by Apexbio Technology LLC
DMSO ≥70mg/mL Water <1.2mg/mL Ethanol ≥70mg/mL by MedChemexpress Co., Ltd.
Soluble in DMSO, not in water by MedKoo Biosciences, Inc.
(25°C) * In vitro DMSO 72 mg/mL (200.84 mM); Ethanol27 mg/mL (75.31 mM); Water<1 mg/mL (<1 mM); In vivo 1% DMSO+30% polyethylene glycol+1% Tween 8030 mg/mL by Selleck Chemicals LLC
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Mechanism and Indication

6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Pracinostat MEI Pharma Inc Acute myelogenous leukemia 2013/10/31 2015/6/30 Phase 2 Clinical
Pracinostat MEI Pharma Inc Myelodysplastic syndrome 2013/6/30 2015/12/31 Phase 2 Clinical
Pracinostat MD Anderson Cancer Center Myelofibrosis 2010/11/30 Phase 2 Clinical
Pracinostat NCIC Clinical Trials Group Sarcoma 2010/3/31 2013/12/31 Phase 2 Clinical
Pracinostat NCIC Clinical Trials Group Hormone refractory prostate cancer 2010/2/28 2012/11/30 Phase 2 Clinical
Pracinostat - Phase 3
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Safety Data of Pracinostat

8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
AOBIOUS INC USA
AbMole BioScience USA
AdooQ BioScience, LLC USA
Apexbio Technology LLC USA
Ark Pharm, Inc. USA
BOC Sciences
BioVision, Inc., USA
Biochempartner Co., Ltd China
CHEMSCENE, LLC 5mg/USD115();10mg/USD210() USA
Cayman Chemical Company USA
Cayman Chemical Company USA
MedChemexpress Co., Ltd. 5mg/USD115();10mg/USD210() USA
MedKoo Biosciences, Inc. USA
ProbeChem
Selleck Chemicals LLC 5mg/USD210(In stock);10mM/1mLIn DMSO/USD300(In stock);10mg/USD370(In stock);50mg/USD870(In stock) USA
Shanghai Haoyuan Chemexpress Co., Ltd. 5mg/USD115();10mg/USD210() China
Target Molecule Corp. 10mg/USD124();25mg/USD248();50mg/USD388() USA
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Related Products

Other Forms of 929016-96-6

Name CAS No Formula MW

Recommended Compounds in HDAC

Name CAS No Formula MW
Nexturastat A 1403783-31-2 C19H23N3O3 341.4
4SC-202 (free base) 910462-43-0 C23H21N5O3S 447.51
Citarinostat 1316215-12-9 C24H26ClN5O3 467.9479
Tenovin 6 (Hydrochloride) 1011301-29-3 C25H35ClN4O2S 491.09
Sodium Butyrate 156-54-7 C4H7NaO2 110.087
Valproic acid (sodium salt) 1069-66-5 C8H15NaO2 166.19
RGFP966 1357389-11-7 C21H19FN4O 362.4
Resminostat (hydrochloride) 1187075-34-8 C16H20ClN3O4S 385.87
TMP195 1314891-22-9 C23H19F3N4O3 456.4172
TMP269 1314890-29-3 C25H21F3N4O3S 514.52
Benzenebutyric acid 1821-12-1 C10H12O2 164.2011
Parthenolide 20554-84-1 C15H20O3 248.32
Tubastatin-A 1252003-15-8 C20H21N3O2 335.4
Sulforaphane 4478-93-7 C6H11NOS2 177.29
Dacinostat 404951-53-7 C22H25N3O3 379.45
Chidamide 743420-02-2 C22H19FN4O2 390.41
CUDC-907 1339928-25-4 C23H24N8O4S 508.55
Sirtinol 410536-97-9 C26H22N2O2 394.47
M344 251456-60-7 C16H25N3O3 307.39
Tubacin 537049-40-4 C41H43N3O7S 721.86

Recommended Compounds in Same Indication

Name CAS No Formula MW
AZD1152 722543-31-9 C26H31FN7O6P 587.54
AZD1152-HQPA 722544-51-6 C26H30FN7O3 507.56
Mocetinostat 726169-73-9 C23H20N6O 396.44
TAK-700 (R-form) 752243-39-3 C18H17N3O2 307.35
Volasertib 755038-65-4 C34H50N8O3 618.81
Olaparib 763113-22-0 C24H23FN4O3 434.46
KX2-391 897016-82-9 C26H29N3O3 431.53
Bicalutamide 90357-06-5 C18H14F4N2O4S 430.37
MLN4924 905579-51-3 C21H25N5O4S 443.52
IDO5L 914471-09-3 C9H7ClFN5O2 271.6356
Enzalutamide 915087-33-1 C21H16F4N4O2S 464.44
Panobinostat 404950-80-7 C21H23N3O2 349.43
Rigosertib 592542-59-1 C21H25NO8S 451.49
ON-019190 (sodium) 1225497-78-8 C21H24NNaO8S 473.4719
Linsitinib 867160-71-2 C26H23N5O 421.49
Fenretinide 65646-68-6 C26H33NO2 391.55
Crenolanib 670220-88-9 C26H29N5O2 443.54
Retaspimycin 857402-23-4 C31H45N3O8 587.7
Retaspimycin (Hydrochloride) 857402-63-2 C31H46ClN3O8 624.17
Bafetinib 859212-16-1 C30H31F3N8O 576.6154
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Route of Synthesis

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References

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More Information

Pracinostat

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